EP0863744A2 - Acide lipoique en compositions a usage local - Google Patents

Acide lipoique en compositions a usage local

Info

Publication number
EP0863744A2
EP0863744A2 EP96946355A EP96946355A EP0863744A2 EP 0863744 A2 EP0863744 A2 EP 0863744A2 EP 96946355 A EP96946355 A EP 96946355A EP 96946355 A EP96946355 A EP 96946355A EP 0863744 A2 EP0863744 A2 EP 0863744A2
Authority
EP
European Patent Office
Prior art keywords
acid
lipoic acid
skin
damage
lipoic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP96946355A
Other languages
German (de)
English (en)
Other versions
EP0863744B1 (fr
EP0863744A3 (fr
EP0863744A4 (fr
Inventor
Nicholas V Perricone
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
N.V. PERRICONE LLC, A DELAWARE LIMITED LIABILITY C
Original Assignee
PERRICONE, Nicholas V
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Application filed by PERRICONE, Nicholas V filed Critical PERRICONE, Nicholas V
Priority to EP05026439A priority Critical patent/EP1690534A3/fr
Publication of EP0863744A3 publication Critical patent/EP0863744A3/fr
Publication of EP0863744A2 publication Critical patent/EP0863744A2/fr
Publication of EP0863744A4 publication Critical patent/EP0863744A4/fr
Application granted granted Critical
Publication of EP0863744B1 publication Critical patent/EP0863744B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/004—Aftersun preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/385—Heterocyclic compounds having sulfur as a ring hetero atom having two or more sulfur atoms in the same ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • This invention relates to the topical application of compositions containing lipoic acid for the prevention and/or treatment of damage to skin, particularly for the treatment or prevention of inflammatory and aging effects from sunlight and chemical damage.
  • Lipoic acid was originally identified as a bacte ⁇ rial growth factor present in the water-soluble fraction of liver and yeast. It was found to be necessary for the oxidative decarboxylation of pyruvic acid by Streptococ ⁇ cus fecalis and for the growth of Te trah y ena gelii , and replaced acetate for the growth of Lactobacillus casei . It has been variously known as acetate replacing factor, protogen A, and pyruvate oxidation factor.
  • LA lipoic acid
  • DHLA dihydrolipoic acid
  • LA has been used in treating liver cirrhosis, atheroschlerosis, and polyneuritis of diabetes mellitus, diseases in which oxidative stress plays a roll ( ibid . ) . It has also been used as an antidote to poison ⁇ ous mushrooms (particularly Amani ta species, Merck Index, 11th ed., 1989, entry 9255) .
  • the antioxidant activity of lipoic acid appears to prevent free radical damage to cells and cell components. Free radical damage is most evident in cellular membranes because of the density of the molecular structure of the membranes. It is currently hypothesized that cell mem ⁇ brane aging leads to all of the various cellular changes seen in aging, such as decreased RNA production, de ⁇ creased protein production, and faulty enzyme action.
  • Inflammation in skin is mediated by several active chemicals and metabolites of arachidonic acid.
  • Arachi ⁇ donic acid is oxidized by cyclo-oxygenase and lipoxygen- ase to active metabolites such as the leukotrienes and 5- and 12- hydroxyeicosatetraenoic acid (HETES) .
  • HETES 5- and 12- hydroxyeicosatetraenoic acid
  • compositions for anti-inflammatory and anti-aging effects observed in skin particularly compositions that are efficient in free radical scavenging in membranes.
  • the present invention provides a method for the pre ⁇ vention and/or treatment of skin inflammation, aging and other skin damage, which comprises topical application to the exposed or affected skin areas of an effective amount of lipoic acid, lipoic acid derivatives or mixtures thereof in a dermatologically acceptable carrier.
  • tocotrienols or derivatives thereof or vitamin E compositions enriched with toco- trienols or tocotrienol derivatives are included in the lipoic acid composition.
  • Ascorbic acid particularly fat-soluble fatty acid esters of ascorbic acid such as ascorbyl palmitate, can, optionally, also be utilized for further enhancing the efficacy of the therapeutic or prophylactic treatment.
  • Other reductants such as ⁇ -hy- droxy acids and the like may also be added to the compo ⁇ sition.
  • the topical composition contains lipoic acid or dihydrolipoic acid or mixtures thereof, ascorbyl palmitate, and toco ⁇ trienol as active ingredients.
  • the lipoic acid (or derivative) is applied in admixture with a dermatologically acceptable carrier or vehicle (e.g., as a lotion, cream, ointment, soap, or the like) so as to facilitate topical application and, in some cases, pro ⁇ vide additional therapeutic effects as might be brought about, e . g. , by moisturizing of the affected skin areas.
  • a dermatologically acceptable carrier or vehicle e.g., as a lotion, cream, ointment, soap, or the like
  • other ingredients particularly ascorbyl palmi- tate and/or tocotrienol, can be advantageously included in the compositions.
  • lipoic acid or derivative thereof ( hereinafter referred to collectively as lipoic for ease of reference) necessary to bring about enhanced preven- tion and/or therapeutic treatment of skin damage is not fixed per se, and necessarily is dependent upon the iden ⁇ tity and form of lipoic acid employed, the amount and type of any additional ingredients used, particulariy those that appear to exhibit synergistic effects (to be discussed more fully below) , tne user's skm type, and, where present, the severity and extent of the patient's pathological skm or hair condition.
  • the lipoic acid cr composition containing it is topically applied effective amounts to skm areas which have been damaged or aged, or which are susceptible to damage, because of inflammation or aging.
  • the composition contains from about 0.25 to about 5 weight %, preferably from about 1% to about 3%, lipoic acid or dihydrolipoic ac d. In one embodiment, 2% lipoic acid is employed.
  • This mvention is based upon the finding that lipoic acid and dihydrolipoic acid are useful for the treatment and prevention of damaged skin. Lipoic acid and its derivatives also augment the efficacy of other ingredients in topical compositions for inflammation, aging and other skin damage .
  • lipoic acid encompasses thioctic acid (1,2-dithiolane-3-pentanoic acid; 1,2-di- thiolane-3-valeric acid) , which has the following general formula:
  • Lipoic acid derivatives include thioctic acid esters, particularly alkyl esters such as fatty acid esters, amides, particularly those isolated from or mim- icking naturally occurring lipoamides, and salts, partic ⁇ ularly alkali metal salts, and specifically includes the reduced form, dihydrolipoic acid. Since lipoic acid is fat- rather than water-soluble, the water-soluble sodium salt is especially useful in embodiments that have an aqueous base. Derivatives may also include those involv ⁇ ing other reactive groups known to those skilled in the art. As used herein, the term "derivatives" includes metabolic precursors of lipoic acid. Where lipoic acid derivatives are employed, they must be functionally equi ⁇ valent to lipoic acid.
  • lipoic acid is fat-soluble. Therefore, lipoic acid preparations can be applied neat to skin areas subject to damage or already damaged. It is an advantage of the invention that the active compound is fatty so that it physically contributes to the lubri ⁇ cation and soothing of affected skin areas.
  • lipoic acid only effective amounts are needed to prevent or treat skin damage, so generally topical application to exposed or affected skin sites is accomplished in association with a carrier, and particu ⁇ larly one in which the active ingredient is soluble per se or is effectively solubilized (e . g. , as an emulsion or microemulsion) . It is necessary that the carrier be inert in the sense of not bringing about a deactivation of the lipoic acid or derivative, and in the sense of not bringing about any adverse effect on the skin areas to which it is applied.
  • Suitable carriers include water, alcohols, oils and the like, chosen for their ability to dissolve or disperse the active ingredients at concentrations of ac ⁇ tive ingredients most suitable for use in the therapeutic treatment. Generally, even low concentrations of active ingredients in a carrier will be suitable, requiring only that more frequent topical application be resorted to. As a practical matter, however, to avoid the need for repeated application, it is desirable that the topically applied composition De formulated to contain at least about 0.25% to about 5% by weight, more preferably from about 1 % to about 3% by weight, lipoic acid or a deriva ⁇ tive thereof, and accordingly, carriers will be chosen which can solubilize or disperse the active ingredients at such concentrations.
  • One efficacious embodiment con- tains about 2% by weight lipoic acid.
  • the carrier for lipoic acid can consist of a relatively simple ⁇ olvent or dispersant such as oils
  • the carrier comprise a compo ⁇ sition more conducive to topical application, and partic- ularly one which will form a film or layer on the skin to which it is applied so as to localize the application and provide some resistance to perspiration and/or one which aids in percutaneous delivery and penetration of the active ingredients into lipid layers.
  • Many such composi- tions are known in the art, and can take the form of lo ⁇ tions, creams, gels or even solid compositions ( e. g. , stick-form preparations) .
  • compositions include lotions containing water and/or alcohols and emollients such as hydrocarbon oils and waxes, silicone oils, hyal- uronic acid, vegetable, animal or marine fats or oils, glyceride derivatives, fatty acids or fatty acid esters or alcohols or alcohol ethers, lanolin and derivatives, polyhydric alcohols or esters, wax esters, sterols, phos ⁇ pholipids and the like, and generally also emulsifiers (nonionic, cationic or anionic) , although some of the emollients inherently possess emulsifying properties.
  • emollients such as hydrocarbon oils and waxes, silicone oils, hyal- uronic acid, vegetable, animal or marine fats or oils, glyceride derivatives, fatty acids or fatty acid esters or alcohols or alcohol ethers, lanolin and derivatives, polyhydric alcohols or esters, wax esters, sterols, pho
  • compositions are referred to herein as dermatologically acceptable carriers.
  • Most preferred for skm are those carriers which are fat-soluble, i . e . , those which can effectively penetrate skm layers and deliver the active lipoic acid to the lipid- ⁇ ch layers of the sk .
  • lipo ⁇ ic acid had a protective effect on components of a lens antioxidant system comprising ascorbate/dehydroascor ⁇ ate (Maitra, et al . , cited above); the same authors suggest ⁇ ed it may be of possible usefulness n the prevention of cataracts.
  • fat-soluble fatty acid esters of ascorbic acid may be added to the lipoic acid composition in some embodiments.
  • the more oxidation-resistant saturated fatty acid esters of ascorbic acid are preferred, includ ⁇ ing, but not limited to, ascorbyl laurate, ascorbyl my- ristate, ascorbyl palmitate, ascorbyl stearate, and as- corbyl behenate.
  • Ascorbyl palmitate is used in one em ⁇ bodiment.
  • fatty acid esters e . g. , ascorbyl stearate
  • compositions having predominantly that ester, e . g. , predominantly stearate are included.
  • the esters may be prepared using hydroge- nated oils or fats, or fractions thereof, and contain small amounts of another ester.
  • Ascorbyl stearate pre ⁇ pared using canola for example, commonly contain about 4% ascorbyl palmitate.
  • Tocotrienol may also be added to the lipoic acid composition, alone or in combination with an ascorbyl fatty acid ester in some embodiments.
  • Dihydrolipoic acid has been shown to enhance vitamin E recycling in other systems ( ibid. ) .
  • tocotrienol encompasses counterparts of tocopherol (vitamin E) that bear unsatu- rated tails, and mclude, but not limited to, ot- , ⁇ - , ⁇ -, and ⁇ -tocotrienols, desmethyl-tocotrienol , didesmethyl- tocotrienol (occurring in sunflower seeds, vegetable oils, barley, brewer's grains, oats, and African vio ⁇ lets) , their synthetic counterparts, their counterparts having methylated or demethylated chroman rings, and mix ⁇ tures thereof.
  • the double bonds may be cis or trans or mixtures thereof.
  • the tocotrienol is isolated from natural sources and added to the formulation as a tocotrienol- enriched vitamine E preparation.
  • synthetic preparations may also be employed as well as mixtures of natural and synthetic vitamin E.
  • Tocotrienol-enriched vitamin E preparations may be obtained by fractionating vitamin E preparations to remove a portion of tocopherols and recover a preparation more highly concentrated in tocotrienol .
  • Useful tocotrienols are natural products isolated, for example, from wheat germ oil, bran, or palm oil using high performance liquid chromatography, or isolated by alcohol extraction and/or molecular distilla ⁇ tion from barley, brewer's grain or oats. As used here ⁇ in, the term "tocotrienols" includes tocotrienol-rich- fractions obtained from these natural products as well as the pure compounds.
  • tocotrienol or tocotrienol-enriched preparations include those con ⁇ taining tocotrienol and, in some cases, tocopherol deriv ⁇ atives, particularly stabilized derivatives.
  • These typi ⁇ cally include derivatives related to the phenolic hydrox- yl functionality, i.e., wherein it is acylated with an organic acid to form an ester.
  • Examples of such stabi ⁇ lized tocotrienols include, but are not limited to, toco ⁇ trienol acetate, tocotrienol succinate, and mixtures thereof.
  • the derivatives may also include those involving other reactive groups known to those skilled in the art. Where tocotrienol derivatives are employed, they must be functionally equivalent to tocotrienol.
  • Preferred derivatives contain both the chromanol nucleus and three double bonds in the hydrocarbon tail .
  • tocotrienol or tocotrienol-en ⁇ riched vitamin E preparations and/or a fat-soluble vita ⁇ min C fatty acid ester, preferably both, in a dermato ⁇ logically acceptable carrier with lipoic acid or a deriv ⁇ ative is especially advantageous in compositions because lipoic acid augments the efficacy of the other ingredi ⁇ ents the composition.
  • the combination of up to three active ingredients readily solubilizes the lipid-rich layers of the skin and together scavenge free radicals involved in aging, inflammation, and other skin damage.
  • lipoic acid and lipoic acid derivatives especially when employed in combination with ascorbyl fatty acid esters and/or tocotrienols, can be postulated as resulting from the antioxidant properties of active ingredients per se, which properties are unex- pectedly retained and provided to a high degree when used in concert with lipoic acid when these are delivered in combination to the skin in an extremely effective manner in an oil phase.
  • the mechanism of the effect is not well understood, but may be related to the anti-oxidant prop- erties of the active compounds and/or their interference with chemical reactions.
  • lipoic acid as an antioxidant, can scavenge free radicals such as the oxygen radicals created by exposure of skin cells to damage, as well as the generation of free radicals produced by normal metabolism extracellularly and mtra ⁇ cellularly.
  • Dihydrolipoic acid for example, as a power- fui antioxidant concentrated in cell membranes, can less ⁇ en erythema by the mechanism of free radical scavenging and chain breaking chemical reactions.
  • Ascorbic acid is a powerful reducing agent that can prevent oxidative damage and regenerate chromanoxyi radicals formed as vitamin E derivatives scavenge radicals, reforming vita ⁇ min E that can scavenge more radicals.
  • Preferred embodi ⁇ ments of this invention harness this synergestic effect.
  • ascorbic acid can increase cyclo-oxy- genase activity in human cells.
  • Cyclo-oxygenase is a key enzyme in the oxidation of arachadonic acid, which leads the formation of prostaglandins which in turn mediate in ⁇ flamma ion.
  • Some embodiments further include ⁇ -hydroxy acid ingredients such as glycolic acid, hydroxymethylglycolic acid, lactic acid, glucuronic acid, galacturonic acid, gluconic acid, glucoheptonic acid, ⁇ -hydroxybutyric acid, ⁇ -hydroxyisobutyric acid, ⁇ -hydroxyvaleric acid, ⁇ r-hy- droxyisovaleric acid, ⁇ -hydroxycaproic acid, ⁇ -isocaproic acid, tartronic acid, tartaric acid, malic acid, hydroxy- glutaric acid, hydroxyadipic acid, hydroxypimelic acid, muric acid, citric acid, isocitric acid, saccharic acid, dihydroxymaleic acid, dihydroxytartaric acid, and dihy- droxyfumaric acid or derivatives of hydroxy acids such as pyruvic acid, methyl pyruvate, ethyl pyruvate, isopropyl pyruvate, benzoylformic
  • lipoic acid and its deriva- tives are also effective in the prevention of cell aging, as are combinations with ascorbic acid fatty acid esters and tocotrienols. All the substances are fat-soluble and disperse within cell membranes, acting as free radical scavengers and neutralizers, and prevent the cross-link- ing of cell membranes that is seen in the aging process. Once the cell membranes are cross-linked, the permeabili ⁇ ty of cell membranes increases, causing an inefficient exchange of nutrients and waste products within the cell . The decreased cell permeability results in increased ionic concentration of potassium, which then causes de ⁇ creased messenger RNA production. The increased ionic concentration also interferes with enzyme activity, as enzymes are very much dependent on ionic concentration for their action.
  • RNA In addition to decreased production of RNA, there is a marked decrease in the production of protein with aging, and therefore the cell cannot repair itself.
  • the altered cellular membranes prevent removal of waste prod- ucts in the cell, such as lipofucin, which is a histolog ⁇ ic characteristic of all aging cells.
  • Lipoic acid and its derivatives by preventing free radical damage to cell membranes and preventing decreased permeability to cells, can theoretically prevent aging of the cell by maintaining proper ionic concentration, proper disposal of waste products, and efficient protein and RNA produc ⁇ tion.
  • Topical application of lipoic acid and its deriva ⁇ tives to skin can thus prevent cell aging, and the effect is pronounced when acting in concert with ascorbyl fatty acid esters and/or tocotrienol.
  • the method of the present invention is particular ⁇ ly useful for the prevention of skin damage which may result from exposure to ultraviolet radiation, but, based upon the likely mechanism of action, also is useful in general for treatment of any radiation-induced skin dam ⁇ age, particularly that associated with free radical re ⁇ lated damage.
  • the topical application of lipoic acid according to the invention can also be effective for chronic administration to prevent the free radical damage seen in the natural aging process of the skin and the free radical damage caused by chronic exposure to sun ⁇ light.
  • Lipoic acid, alone or with tocotrienol and/or ascorbyl fatty acid esters can thus be added to dermato ⁇ logical creams and emollients as well as to commercial suncreens to enhance their anti-aging and anti-cancer activity.
  • compositions of the invention exhibit efficacy when applied to a variety of skin dam ⁇ aged conditions, including dry skin, psoriasis, and der ⁇ matitis (contact, irritant, and allergic) .
  • compositions of the invention can also be used as a treatment after burn.
  • the composition is topically applied to the affected skin areas in a predetermined or as-needed regimen to bring about improvement, it generally being the case that gradual improvement is noted with each successive application. Insofar as has been determined based upon clinical studies to date, no adverse side effects are encountered.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Birds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
EP96946355A 1995-09-20 1996-08-12 Acide lipoique en compositions a usage local Expired - Lifetime EP0863744B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP05026439A EP1690534A3 (fr) 1995-09-20 1996-08-12 Acide lipoique en compositions à usage local

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/531,290 US5709868A (en) 1995-09-20 1995-09-20 Lipoic acid in topical compositions
US531290 1995-09-20
PCT/US1996/013098 WO1997010808A1 (fr) 1995-09-20 1996-08-12 Acide lipoique en compositions a usage local

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP05026439A Division EP1690534A3 (fr) 1995-09-20 1996-08-12 Acide lipoique en compositions à usage local

Publications (4)

Publication Number Publication Date
EP0863744A3 EP0863744A3 (fr) 1997-03-27
EP0863744A2 true EP0863744A2 (fr) 1998-09-16
EP0863744A4 EP0863744A4 (fr) 2002-04-03
EP0863744B1 EP0863744B1 (fr) 2006-07-12

Family

ID=24117034

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Application Number Title Priority Date Filing Date
EP05026439A Withdrawn EP1690534A3 (fr) 1995-09-20 1996-08-12 Acide lipoique en compositions à usage local
EP96946355A Expired - Lifetime EP0863744B1 (fr) 1995-09-20 1996-08-12 Acide lipoique en compositions a usage local

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Application Number Title Priority Date Filing Date
EP05026439A Withdrawn EP1690534A3 (fr) 1995-09-20 1996-08-12 Acide lipoique en compositions à usage local

Country Status (9)

Country Link
US (1) US5709868A (fr)
EP (2) EP1690534A3 (fr)
JP (1) JPH11512452A (fr)
AT (1) ATE332687T1 (fr)
CA (1) CA2232583C (fr)
DE (1) DE69636342T2 (fr)
ES (1) ES2270442T3 (fr)
PT (1) PT863744E (fr)
WO (1) WO1997010808A1 (fr)

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US6296861B1 (en) * 1999-05-03 2001-10-02 Nicholas V. Perricone Treatment of skin damage using conjugated linoleic acid and ascorbyl fatty acid esters
WO2001021208A1 (fr) 1999-09-23 2001-03-29 Juvenon Corporation Supplement nutritionnel fournissant une energie et une endurance accrues
US6562869B1 (en) 1999-09-23 2003-05-13 Juvenon, Inc. Nutritional supplement for increased energy and stamina
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US6555573B2 (en) * 2000-12-21 2003-04-29 The Quigley Corporation Method and composition for the topical treatment of diabetic neuropathy
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PT863744E (pt) 2006-11-30
CA2232583C (fr) 2003-04-08
ATE332687T1 (de) 2006-08-15
DE69636342D1 (de) 2006-08-24
CA2232583A1 (fr) 1997-03-27
EP1690534A3 (fr) 2007-07-25
US5709868A (en) 1998-01-20
EP0863744B1 (fr) 2006-07-12
EP1690534A2 (fr) 2006-08-16
ES2270442T3 (es) 2007-04-01
JPH11512452A (ja) 1999-10-26
DE69636342T2 (de) 2007-08-02
WO1997010808A1 (fr) 1997-03-27
EP0863744A4 (fr) 2002-04-03

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